The weirdest stories about Frank Sinatra

Mandi Goodier

In celebration of the centenary of his birth, we're rounding up some of the weirdest stories from the career of Old Blue Eyes.

'My Way’ a song both hated and cursed

First of all, Old Blue Eyes hated ‘My Way’, which is surprising to hear considering it was his most iconic song. It was sung and penned for his retirement in 1969. A tremendous good-bye.

Of course the addictive limelight shone down on him again, as he returned some years later—surprised to find it had unwittingly become his trademark number. He was never quiet about his hatred of the song, and regularly made his feelings known.

 “And of course, the time comes now for the torturous moment—not for you, but for me.”

It’s unknown why he felt so fiercely agitated by the song. Whether it was the fact that it was written by an 18-year-old—and, hey, what do they know about life—or it was the fact that Sinatra was actually a modest guy, never one to brag about himself. Or, perhaps he was aware of something darker at play…

 

The ‘My Way Killings’

My Way Karaoke
 Image via New York Times

In the Philippines the song is banned in most karaoke bars, where the song has been known to cause riots and deaths.

On more than one occasion, people have been shot while performing the song. At first it was considered coincidence, after all, it’s a popular song in the Philippines, sung so often that of course the odd person is bound to die while performing it. But are the murder rates in the Philippines really that high?

However it started, the song became considered so dangerous that many bars started to ban it, stating that it caused ‘videoke rage’. In 2007, a 29-year-old was even shot by a security guard because he was singing it out of tune.

Rodolfo Gregorio, 63, a karaoke singer in the Philippine city of General Santos, said: "The trouble with 'My Way' is that everyone knows it and everyone has an opinion. You can get killed."

 

Scooby-dooby-doo

Scooby Doo
Image via Legion of Leia 

1969, it wasn’t just the year that Sinatra planned to retire (only to return for another 25 years), it was also the Summer of Love which gave birth to those pesky Scooby-doo kids.

When it was pitched to CBS, it was a little different. The group were a groovy band who played far out music and solved mysteries alongside their dog, named Too Much.

CBS were not keen on the format. It was too scary. But inspiration struck the CBS children’s programming head Fred Silverman while listening to Sinatra. Towards the end of the song, ‘Strangers in the Night’, Frank enters into a light scat, “Shooby-dooby-doo,” and with that Too Much was renamed Scooby Doo and became the star of the show.

 

Sinatra’s FBI file

Frank Sinatra
Image via The Smoking Gun

It isn’t the file itself that’s weird—despite connections to the mob and a minor misdemeanour for being overly amorous—it’s why it was started in the first place.

In 1943 J. Edgar Hoover received a rather paranoid letter from an anonymous tipster reading as follows:

"Dear Sir:
The other day I turned on a Frank Sinatra program and I noted the shrill whistling sound, created supposedly by a bunch of girls cheering. Last night as I heard Lucky Strike produce more of this same hysteria I thought: how easy it would be for certain-minded manufacturers to create another Hitler here in America through the influence of mass-hysteria! I believe that those who are using this shrill whistling sound are aware that it is similar to that which produced Hitler. That they intend to get a Hitler in by first planting in the minds of the people that men like Frank Sinatra are O.K. therefore this future Hitler will be O.K.

J. Edgar Hoover, already wary of the young singer, responded by validating his concern and opened a file that spanned 50 decades. But why would he listen to such war-time hysteria?

It’s quite simple really, it was a relationship born out of fear: that the youth would be corrupted by a menace who went against everything Hoover stood for, politically, socially and legally.

Sinatra was a:

  • Traveller who strived for racial tolerance and consorted with Communists
  • He was a mob associate
  • And he regularly crooned before the nation's youth

It was everything the early FBI wanted to stamp out. It was through a similar fear of youth in revolt that he also opened a file on John Lennon in the 1970s.

When Sinatra died in 1998, the files were closed and released. Much to everyone’s surprise, and in spite of 6-inches-thick documentation, there were no bombshells whatsoever.

 

Frank Sinatra: the greatest action hero in the world?

Frank Sinatra
Gif via The Manchurian Candidate

Arnold Schwarznegger. Bruce Willis. Liam Neeson. Frank Sinatra?

Believe it or not, Sinatra could have fit right in among those action heroes if fate had dealt him a slightly different hand.

Indeed, Sinatra saw some action in the movie The Manchurian Candidate, but it would be this film that would make and then quite literally break his action movie career.

During a karate fight scene alongside actor Henry Silva, the crooner threw a karate chop, striking his hand on a wooden table, breaking his little finger.

Minor injury? Well, nine years later, Warner Brothers invited Sinatra to play the starring role in Dirty Harry, but his injury prevented him from wielding Harry’s 44 magnum. Instead, that legendary role went to the legendary Clint Eastwood.

But this was not the end! Some 16 years after that, at the age of 73, he was offered the lead role in Die Hard. Yippee ki ay.

 

Human, all too human

Frank Sinatra
Image via Hooked On

Women adored him, men wanted to be him, 100 years after his birth and he still has an abundance of fans. But Frank, like the rest of us, was a mere mortal, who suffered insecurities.

After a traumatic birth, Sintara was scarred on the left side of his face by forceps. Throughout his teens he had suffered from acne, leaving pitted cheeks. Naturally Frank grew up a little self-conscious.

He used makeup to cover his scars and hated being photographed on the left side.

At 5’6 Sinatra wasn’t exactly tiny, but he clearly also felt an insecurity here too. Throughout the years he gave various heights to those who enquired: 5’9, 5’10, 5’11. Both his assistant and his biographer claimed he wore elevated shoes to boost him to 5’9.

But perhaps one of the saddest moments of Sinatra’s life came in the early 1950s. Sinatra would have been in his late 30s and his career took a dive.

While walking through time square one evening he saw mobs of girls waiting to watch the younger, newer, singing sensation Eddie Fisher. The sight cut Sinatra deep, affirming his worst fear: that he was washed up.

Sinatra returned home, put his head i the stove and turned on the gas. Fortunately, his manager found him before it was too late. Frank’s feelings about himself and his career were wrong, there was so much more left in him.